(S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester
• CAS No.: 150903-48-3
• Molecular Formula: C₂₉H₃₁NO₆S
• Molecular Weight: 521.634

Synonyms:(S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester

Chemical Property of (S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester

There total 9 articles about (S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1-p-Nitro-phenylethyl)-malonsaeurediethylester (37556-09-5) → (S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester (150903-48-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / KOH / ethanol / 0 - 20 °C

2: Et₂NH / H₂O / 48 h / Ambient temperature

3: aq. NaOH / acetone / 0 - 20 °C

4: 100 percent / CH₂Cl₂ / 48 h / 40 - 80 °C

5: 59 percent / Et₃N, 1-hydroxybenzotriazole, DCC / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

6: 85 percent / H₂ / Pd/C / methanol

7: 1.) NaNO₂, H₂SO₄, 2.) aq. H₂SO₄ / 1.) dioxane, water, 5 deg C, 5 min, 2.) dioxane, reflux, 5 min

With potassium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; benzotriazol-1-ol; diethylamine; triethylamine; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1021/jm00034a005

Reference yield:

diethyl (1-phenylethyl)malonate (14618-12-3) → (S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester (150903-48-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 84 percent / conc. H₂SO₄, KNO₃ / 2 h / -10 °C

2: 93 percent / KOH / ethanol / 0 - 20 °C

3: Et₂NH / H₂O / 48 h / Ambient temperature

4: aq. NaOH / acetone / 0 - 20 °C

5: 100 percent / CH₂Cl₂ / 48 h / 40 - 80 °C

6: 59 percent / Et₃N, 1-hydroxybenzotriazole, DCC / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

7: 85 percent / H₂ / Pd/C / methanol

8: 1.) NaNO₂, H₂SO₄, 2.) aq. H₂SO₄ / 1.) dioxane, water, 5 deg C, 5 min, 2.) dioxane, reflux, 5 min

With potassium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; benzotriazol-1-ol; potassium nitrate; diethylamine; triethylamine; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1021/jm00034a005

Reference yield:

(1-bromoethyl)benzne (585-71-7,38661-81-3) → (S)-2-[2-Acetylsulfanylmethyl-3-(4-hydroxy-phenyl)-butyrylamino]-3-(4-hydroxy-phenyl)-propionic acid benzyl ester (150903-48-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) EtONa / 1.) EtOH, 0 deg C, 15 min, 2.) EtOH, 40 deg C, overnight

2: 84 percent / conc. H₂SO₄, KNO₃ / 2 h / -10 °C

3: 93 percent / KOH / ethanol / 0 - 20 °C

4: Et₂NH / H₂O / 48 h / Ambient temperature

5: aq. NaOH / acetone / 0 - 20 °C

6: 100 percent / CH₂Cl₂ / 48 h / 40 - 80 °C

7: 59 percent / Et₃N, 1-hydroxybenzotriazole, DCC / tetrahydrofuran; CH₂Cl₂ / Ambient temperature

8: 85 percent / H₂ / Pd/C / methanol

9: 1.) NaNO₂, H₂SO₄, 2.) aq. H₂SO₄ / 1.) dioxane, water, 5 deg C, 5 min, 2.) dioxane, reflux, 5 min

With potassium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; sodium ethanolate; benzotriazol-1-ol; potassium nitrate; diethylamine; triethylamine; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;

DOI:10.1021/jm00034a005

upstream raw materials:

diethyl (1-phenylethyl)malonate

(1-p-Nitro-phenylethyl)-malonsaeurediethylester

(1-bromoethyl)benzne

2-Methylene-3-(4-nitro-phenyl)-butyric acid

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